Sales Development Representative (SDR) 2025

Sales Development Representative

Position Overview

Wholesail is seeking a motivated Sales Development Representative (SDR) to join our growing team. As an SDR, you will be the initial point of contact for finance and operations leaders at SMB, mid-market, and enterprise organizations. Your primary responsibility will be to identify new business opportunities, engage with prospective customers, and effectively communicate how Wholesail can address their pain points in accounts receivable, payment operations, and credit management. This foundational sales role is designed to equip you with the skills necessary for strategic, high-impact selling, working closely with Account Executives and sales leadership to build a robust pipeline.

About Wholesail

Wholesail empowers over 400 wholesalers to confidently manage payment risk without compromising customer relationships or growth. Our platform integrates credit onboarding tools, automated AR communications, a payment portal, and accounts receivable workflow tools. Wholesail helps customers get paid 35% faster, streamline AR processes, reduce credit card costs, and enhance the customer experience.

Founded by serial entrepreneurs, Wholesail aims to foster enduring relationships between food and beverage wholesalers and their restaurant and grocery buyers. The company is well-funded, supported by numerous venture capital firms and angel investors with expertise in fintech, payments, SMB marketplaces, and distribution, including early team members from industry leaders like Stripe, Square, Dropbox, Yelp, OpenTable, and Everlane.

Website: www.paywholesail.com

Responsibilities

• Utilize modern sales tools to identify businesses within Wholesail’s ideal customer profile across various business sizes and markets.
• Engage with prospects at scale through cold calling, emailing, and social selling (e.g., LinkedIn).
• Reach out to businesses in your pipeline at scale through cold calling, emailing, and social selling.
• Promote urgency through a solutions-based sales approach, identifying business challenges and providing targeted value on how Wholesail can help.
• Partner directly with Account Executives to identify winning strategies for outbound prospecting.
• Develop a deep understanding of Wholesail’s value proposition and products to effectively communicate their benefits to prospects.
• Adapt and think on your feet to refine your approach to prospects and find creative solutions to engage decision-makers.
• Grow your career in sales through frequent developmental opportunities and mentorship from the Account Executive team.
• Consistently attain and exceed monthly quotas.

Requirements

• Strong interest in building a career in SaaS sales.
• Clear and confident communication skills, both verbal and written.
• Interest in business operations, finance, or the food and beverage industry.
• Comfortable making cold calls and writing prospecting emails.
• Organized and detail-oriented, with the ability to manage a high-volume outreach pipeline.
• Self-motivated and eager to learn in a fast-paced environment.
• Team player who values feedback and coaching.
• Experience with or willingness to learn modern sales and automation tools (e.g., Salesforce, SalesLoft, Gong, ZoomInfo, and AI-powered prospecting platforms).
• A BA/BS degree or equivalent practical experience.
• Prior SDR or outbound sales experience is a plus.

Compensation & Benefits

• Salary: $50K-$70K base + $20K-$30K bonus opportunity (based on experience).
• Benefits:
  • Work with experienced tech startup founders and a customer-centric team.
  • Medical, dental, and vision insurance.
  • Short-term disability insurance.
  • 401K.
  • $100 per month phone stipend.
  • $50 reimbursable monthly expense for work-from-home internet.
  • 15 PTO (Paid Time Off) days per year.
  • 5 paid sick days per year.

Employment Type

• [Employment Type not specified]

Location Type

• [Location Type not specified]